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Abstract:

The TRA (3-[2-aminoethyl]indole) is an important neurotransmitter with a close structural and chemical similarity to the neurotransmitter serotonin (5-hydroxytryptamine), and to melatonin (5-methoxy-N-acetyltryptamine), which plays a key role in daily human behavior. Moreover, TRA, and other indolic compounds are very efficient antioxidants. In this work the conformational space of TRA was scanned in aqueous solution, simulating the solvent by the polarizable continuum model. Geometry optimizations were performed at B3LYP/6-31+G**level. Electronic distributions were analyzed at a better calculation level, thus improving the basis set (6-311++G**). A topological study based on Bader's theory (atoms in molecules) and natural bond orbital (NBO) framework was performed. Structural changes found in solution were related with charge delocalization mechanisms, which explained the changes in the conformational relative population in aqueous phase. Solvent effects on molecular electrostatic potential (MEPs) were also quantified and rationalized through charge delocalization mechanisms, thus connecting changes in MEPs with changes in structure, bond polarization, orbital bonding populations, natural charges, and bond topological properties. Moreover, polarizabilities and dipolar moments were calculated. All conformers were taken into account. Our results are the first prediction of TRA polarizabilities. The results reported contribute to the understanding of the structure, stability and reactivity of TRA and other indole derivatives. © 2012 Springer-Verlag Berlin Heidelberg.

Registro:

Documento: Artículo
Título:Aqueous solvent effects on the conformational space of tryptamine. Structural and electronic analysis
Autor:Lobayan, R.M.; Schmit, M.C.P.; Jubert, A.H.; Vitale, A.
Filiación:Instituto de Investigaciones Científicas (IDIC), Facultad de Ingeniería, Universidad de la Cuenca Del Plata, Lavalle 50, 3400 Corrientes, Argentina
CEQUINOR Facultad de Ciencias Exactas, Facultad de Ingeniería, Universidad Nacional de la Plata, C:C: 962, 1900 La Plata, Argentina
IBIMOL (Ex PRALIB)(UBA CONICET), Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956, C1113AAD Buenos Aires, Argentina
Departamento de Física, Facultad de Ciencias Exactas y Naturales y Agrimensura, Universidad Nacional Del Nordeste, Avda. Libertad 5300, 3400 Corrientes, Argentina
Idioma: Inglés
Palabras clave:(3-[2-aminoethyl]indole); Antioxidants; Aqueous solvent effect; Atoms in Molecules; Density functional theory; Molecular dipole moment; Molecular polarizability; Natural bond prbital analysis; PCM model; TRA; Tryptamine; 3 [2 aminoethyl]indole; indole derivative; tryptamine; unclassified drug; aqueous solution; article; chemical bond; chemical structure; priority journal; Antioxidants; Humans; Hydrogen Bonding; Melatonin; Models, Molecular; Molecular Conformation; Neurotransmitter Agents; Serotonin; Solutions; Solvents; Static Electricity; Thermodynamics; Tryptamines; Water
Año:2013
Volumen:19
Número:3
Página de inicio:1109
Página de fin:1123
DOI: http://dx.doi.org/10.1007/s00894-012-1650-6
Título revista:Journal of Molecular Modeling
Título revista abreviado:J. Mol. Model.
ISSN:16102940
CODEN:JMMOF
CAS:tryptamine, 343-94-2, 61-54-1; Antioxidants; Melatonin, 73-31-4; Neurotransmitter Agents; Serotonin, 50-67-9; Solutions; Solvents; Tryptamines; Water, 7732-18-5; tryptamine, 422ZU9N5TV
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_16102940_v19_n3_p1109_Lobayan

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Citas:

---------- APA ----------
Lobayan, R.M., Schmit, M.C.P., Jubert, A.H. & Vitale, A. (2013) . Aqueous solvent effects on the conformational space of tryptamine. Structural and electronic analysis. Journal of Molecular Modeling, 19(3), 1109-1123.
http://dx.doi.org/10.1007/s00894-012-1650-6
---------- CHICAGO ----------
Lobayan, R.M., Schmit, M.C.P., Jubert, A.H., Vitale, A. "Aqueous solvent effects on the conformational space of tryptamine. Structural and electronic analysis" . Journal of Molecular Modeling 19, no. 3 (2013) : 1109-1123.
http://dx.doi.org/10.1007/s00894-012-1650-6
---------- MLA ----------
Lobayan, R.M., Schmit, M.C.P., Jubert, A.H., Vitale, A. "Aqueous solvent effects on the conformational space of tryptamine. Structural and electronic analysis" . Journal of Molecular Modeling, vol. 19, no. 3, 2013, pp. 1109-1123.
http://dx.doi.org/10.1007/s00894-012-1650-6
---------- VANCOUVER ----------
Lobayan, R.M., Schmit, M.C.P., Jubert, A.H., Vitale, A. Aqueous solvent effects on the conformational space of tryptamine. Structural and electronic analysis. J. Mol. Model. 2013;19(3):1109-1123.
http://dx.doi.org/10.1007/s00894-012-1650-6